N-Acetyl-L-Cysteine → 2-(Pyrimidin-2-yl)pyrimidine-5-carboxylic acid

HRID 2382031ノート

反応式

HRID 2382031 の反応式
[C:1]([C:3]1[N:8]=[CH:7][CH:6]=[CH:5][N:4]=1)#[N:2].C([NH:12][C@H](C(O)=O)CS)(=O)C.C([O-])(=O)C.[NH4+].C([O:26][C:27]([C:29]([C:32](=O)C)=[CH:30][O-])=[O:28])C.[Na+].[OH-].[Na+]>O.CO>[N:2]1[CH:30]=[C:29]([C:27]([OH:26])=[O:28])[CH:32]=[N:12][C:1]=1[C:3]1[N:8]=[CH:7][CH:6]=[CH:5][N:4]=1

参加物

8

反応物 5

HCID 12035N-Acetyl-L-CysteineHCID 14798Sodium HydroxideHCID 517165Ammonium AcetateHCID 27579792-CyanopyrimidineHCID 86639377Sodium 2-ethoxycarbonyl-3-oxo-but-1-en-1-olate

生成物 1

HCID 533964792-(Pyrimidin-2-yl)pyrimidine-5-carboxylic acid収率 59%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒2 回HCID 962Water溶媒

反応条件

温度
110 °C

実験手順

A pressure vessel is charged with 2-cyanopyrimidine (7.88 g, 75 mmol), N-acetyl cysteine (1.22 g, 7.5 mmol), ammonium acetate (6.93 g, 90 mmol), and MeOH (75 mL). The vessel is sealed and heated at 110° C. for 1.5 h, and then cooled to rt. To the reaction mixture is added sodium 2-ethoxycarbonyl-3-oxo-but-1-en-1-olate (17 g, 86.25 mmol) and MeOH (75 mL). The mixture is heated to reflux for 1.5 h and then cooled to rt. NaOH (6 g, 150 mmol) and water (80 mL) are added. The mixture is stirred for 30 min or until LC-MS indicates complete hydrolysis of the intermediate ester. The pH of the reaction mixture is adjusted to 3 with concentrated (12 M) aqueous HCl. MeOH is evaporated in vacuo, and the resulting precipitate is collected via filtration and washed with minimal chilled water to yield [2,2′]bipyrimidinyl-5-carboxylic acid (59%). MS: 203 (M+H); 1H NMR (300 MHz, CDCl3): δ=7.71 (t, 1H), 9.06 (d, 2H), 9.40 (s, 2H).

後処理

  1. customThe vessel is sealed
  2. temperaturecooled to rt
  3. temperatureThe mixture is heated
  4. temperatureto reflux for 1.5 h
  5. temperaturecooled to rt
  6. concentrationwith concentrated (12 M) aqueous HCl
  7. customMeOH is evaporated in vacuo
  8. filtrationthe resulting precipitate is collected via filtration
  9. washwashed
  10. temperaturewith minimal chilled water

出典と根拠

ORDレコード
ord-aed5129288cf4791beb75f681a9aba11
出典データセット
uspto-grants-2012_09
特許番号
US08258130B2

反応ノート

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